CA1039000A - Method for preparation of methacrylate and acrylate polymers and copolymers by anionic polymerization - Google Patents
Method for preparation of methacrylate and acrylate polymers and copolymers by anionic polymerizationInfo
- Publication number
- CA1039000A CA1039000A CA214,514A CA214514A CA1039000A CA 1039000 A CA1039000 A CA 1039000A CA 214514 A CA214514 A CA 214514A CA 1039000 A CA1039000 A CA 1039000A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- alpha
- monomer
- metallo
- polymerization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000010539 anionic addition polymerization reaction Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title claims abstract description 8
- 229920001577 copolymer Polymers 0.000 title claims description 22
- 229920000058 polyacrylate Polymers 0.000 title claims description 4
- 239000000178 monomer Substances 0.000 claims abstract description 47
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 42
- -1 alkali metal alkoxide Chemical class 0.000 claims abstract description 37
- 150000002148 esters Chemical class 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000003999 initiator Substances 0.000 claims abstract description 22
- 230000000977 initiatory effect Effects 0.000 claims abstract description 18
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 15
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 12
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 11
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 8
- 230000001965 increasing effect Effects 0.000 claims abstract description 7
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 6
- 150000003857 carboxamides Chemical class 0.000 claims abstract description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 4
- 159000000011 group IA salts Chemical class 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract 2
- 125000004185 ester group Chemical group 0.000 claims abstract 2
- 239000011734 sodium Substances 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Substances [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 238000012661 block copolymerization Methods 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 abstract description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000129 anionic group Chemical group 0.000 abstract description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 3
- 150000002170 ethers Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 126
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 25
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 19
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 15
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 5
- 229940063557 methacrylate Drugs 0.000 description 5
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002900 organolithium compounds Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 150000003112 potassium compounds Chemical class 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000237074 Centris Species 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- WHLPIOPUASGRQN-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C WHLPIOPUASGRQN-UHFFFAOYSA-N 0.000 description 1
- PKEQAFCDFSRQAN-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;prop-2-enenitrile Chemical compound C=CC#N.CCCCOC(=O)C(C)=C PKEQAFCDFSRQAN-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 102220053804 rs727503299 Human genes 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS813673A CS168303B1 (is") | 1973-11-26 | 1973-11-26 | |
| CS373474A CS176528B1 (is") | 1974-05-24 | 1974-05-24 | |
| CS469074A CS173270B1 (is") | 1974-07-03 | 1974-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1039000A true CA1039000A (en) | 1978-09-19 |
Family
ID=27179433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA214,514A Expired CA1039000A (en) | 1973-11-26 | 1974-11-25 | Method for preparation of methacrylate and acrylate polymers and copolymers by anionic polymerization |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4056580A (is") |
| JP (1) | JPS5089490A (is") |
| CA (1) | CA1039000A (is") |
| DE (1) | DE2455717A1 (is") |
| FR (1) | FR2252360B1 (is") |
| GB (1) | GB1477373A (is") |
| IT (1) | IT1025975B (is") |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1469090A (en) * | 1974-06-27 | 1977-03-30 | Ceskoslovenska Akademie Ved | Polymers of acyloxyalkyl methacrylates method for their preparation |
| US4218552A (en) * | 1974-06-27 | 1980-08-19 | Ceskoslovenska Akademie Ved | Polymers of pivaloyloxyalkyl methacrylates, method for their preparation and modification |
| CS196919B1 (en) * | 1977-12-29 | 1980-04-30 | Lubomir Lochmann | Process for preparing polymers and copolymers of vinylic monomers |
| US4356288A (en) * | 1979-03-05 | 1982-10-26 | Rohm And Haas Company | Novel polymers of alkyl acrylates |
| US4246370A (en) * | 1979-03-05 | 1981-01-20 | Rohm And Haas Company | Use of novel polymers of alkyl acrylates |
| US4388448A (en) * | 1981-02-23 | 1983-06-14 | E. I. Du Pont De Nemours And Company | Glycidyl methacrylate polymers, their preparation and solvolysis products |
| DE3803406C2 (de) * | 1988-02-05 | 1997-02-13 | Roehm Gmbh | Verfahren zur Trennung von Methanol-Methylmethacrylat-Mischungen |
| US5629393A (en) * | 1989-06-05 | 1997-05-13 | Elf Atochem S.A. | Initiating process and system for the anionic polymerization of acrylic monomers |
| JP3099346B2 (ja) * | 1990-06-08 | 2000-10-16 | 大日本インキ化学工業株式会社 | アニオンリビングポリマーの製造方法およびこの製造方法で得られたアニオンリビングポリマーを用いるポリマーの製造方法 |
| US5241002A (en) * | 1990-06-08 | 1993-08-31 | Dainippon Ink And Chemicals, Ltd. | Anionic living polymers, their derivatives and composition comprising them |
| US6215018B1 (en) | 1997-08-11 | 2001-04-10 | Ciba Specialty Chemicals Corporation | Acrylate monomer preparation using alkali metal alkoxides as ester interchange catalysts and bromide salt polymerization inhibitors |
| US6008404A (en) * | 1997-08-11 | 1999-12-28 | Ciba Specialty Chemicals Corporation | Acrylate monomer preparation using alkali metal alkoxides as ester interchange catalysts and bromide salt polymerization inhibitors |
| CN107163183A (zh) * | 2017-04-21 | 2017-09-15 | 苏州博纳化学科技有限公司 | 丙烯酸酯‑丙烯腈共聚物的分散剂及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2841574A (en) * | 1954-02-01 | 1958-07-01 | Ethyl Corp | Anionic polymerization process |
| US3761529A (en) * | 1969-07-28 | 1973-09-25 | Ceskoslovenska Akademie Ved | Method of purifying alkali metal alkoxides |
| CS166982B1 (is") | 1973-05-07 | 1976-03-29 |
-
1974
- 1974-11-21 US US05/525,854 patent/US4056580A/en not_active Expired - Lifetime
- 1974-11-22 GB GB5061274A patent/GB1477373A/en not_active Expired
- 1974-11-25 DE DE19742455717 patent/DE2455717A1/de not_active Withdrawn
- 1974-11-25 IT IT29792/74A patent/IT1025975B/it active
- 1974-11-25 JP JP49134450A patent/JPS5089490A/ja active Pending
- 1974-11-25 CA CA214,514A patent/CA1039000A/en not_active Expired
- 1974-11-26 FR FR7438698A patent/FR2252360B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2252360B1 (is") | 1978-06-16 |
| FR2252360A1 (is") | 1975-06-20 |
| GB1477373A (en) | 1977-06-22 |
| US4056580A (en) | 1977-11-01 |
| IT1025975B (it) | 1978-08-30 |
| JPS5089490A (is") | 1975-07-17 |
| DE2455717A1 (de) | 1975-05-28 |
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